Water → HCID 86642396, compound

HRID 1951973Notes

Reaction equation

HRID 1951973 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:9]1([O:19][CH3:20])[C:10](=[CH:12][CH:13]=[C:14]([CH:18]=1)[CH2:15][CH:16]=[CH2:17])[OH:11].C(N(CC)CC)C.O>ClCCl>[CH2:1]([S:5]([O:11][C:10]1[CH:12]=[CH:13][C:14]([CH2:15][CH:16]=[CH2:17])=[CH:18][C:9]=1[O:19][CH3:20])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3314EugenolHCID 8471TriethylamineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 86642396HCID 86642396, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

13 ml (100 mmol) of butanesulfonyl chloride is added dropwise to a solution of 15 g (90 mmol) of eugenol and 16 ml (110 mmol) of triethylamine in 150 ml of dichloromethane previously cooled to −20° C., then the reaction mixture is stirred for 4 hours at room temperature. After adding 50 ml of water and extracting with dichloromethane, the organic phase is dried over sodium sulfate, filtered and evaporated. The raw residue is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 90/10. 24.3 g (74%) of 4-allyl-2-methoxy-phenyl 1-butane sulfonate is obtained in the form of a yellow oil.

Workup

  1. extractionextracting with dichloromethane
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe raw residue is purified by silica column chromatography
  6. washeluted with a heptane/ethyl acetate mixture 90/10

Sources & evidence

ORD record
ord-b2fb9f50f3d949e59894bc530a3e7d95
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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